2-METHYLUNDECANAL Property

Boiling point:

171 °C(lit.)

Density 

0.83 g/mL at 25 °C(lit.)

vapor pressure 

2.4Pa at 20℃

FEMA 

2749 | 2-METHYLUNDECANAL

refractive index 

n20/D 1.432(lit.)

Flash point:

200 °F

Odor

at 1.00 % in dipropylene glycol. fresh amber aldehydic moss citrus tuberose metallic waxy coumarinic

Odor Type

aldehydic

Water Solubility 

1.3mg/L at 20℃

JECFA Number

275

InChI

InChI=1S/C12H24O/c1-3-4-5-6-7-8-9-10-12(2)11-13/h11-12H,3-10H2,1-2H3

InChIKey

NFAVNWJJYQAGNB-UHFFFAOYSA-N

SMILES

C(=O)C(C)CCCCCCCCC

LogP

4.9 at 35℃

CAS DataBase Reference

110-41-8(CAS DataBase Reference)

EPA Substance Registry System

Undecanal, 2-methyl- (110-41-8)

Safety

WGK Germany 

1

RTECS 

YQ1509000

Toxicity

The acute oral LD₅₀ value was reported as > 5 g/kg in the rat . The acute dermal LD₅₀ for sample no. 71-16 was reported to be > 10 g/kg in the rabbit

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

2-METHYLUNDECANAL Chemical Properties,Usage,Production

Description

2-Methylundecanal has a characteristic fatty odor assuming a floral note on dilution. It has an acrid, fatty unpleasant flavor at high levels. At low levels, the flavor is honey- and nut-like. It may be prepared by cracking the corresponding glycidic acid; from α-nonyl acrolein; from methyl nonyl ketone and ethyl monochloroacetate in the presence of sodium ethylate.

Chemical Properties

2-Methylundecanal has a characteristic fatty odor assuming a floral note on dilution. At high levels, it has an acrid, fatty, unpleasant flavor. At low levels, the flavor is honey and nut-like.

Chemical Properties

clear colourless to yellowish liquid

Occurrence

Reported found in kumquat peel oil.

Uses

Perfumery, flavoring.

Preparation

2-Methylundecanal is reported as being found in nature. It is a colorless liquid, with an odor markedly different from that of the isomeric dodecanal. It has a fatty odor with incense and ambergris notes.
2-Methylundecanal is produced by two routes:
1) 2-Undecanone is converted into its glycidate by reaction with an alkyl chloroacetate. Saponification of the glycidate, followed by decarboxylation, yields 2-methylundecanal.
2) The second synthesis is based on the conversion of undecanal into 2- methyleneundecanal by reaction with formaldehyde in the presence of catalytic amounts of amines. Hydrogenation of 2-methyleneundecanal yields methylnonylacetaldehyde (MNA). A convenient process starts from 1-decene: hydroformylation gives a mixture consisting mainly of undecanal and 2-methyldecanal. Reaction of the crude product with formaldehyde in the presence of dibutylamine yields a mixture containing over 50% 2-methyleneundecanal. After hydrogenation of the double bond, pure 2-methylundecanal is separated from the by-products by fractional distillation.
In comparison with other fatty aldehydes, 2-methylundecanal is used in perfumery in rather large amounts to impart conifer notes, particularly fir impressions, but frequently also in fantasy compositions.

Taste threshold values

Taste characteristics at 2 ppm: waxy, fatty, metallic with a citrus nuance.

Flammability and Explosibility

Non flammable

Safety Profile

Low toxicity by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

By cracking the corresponding glycidic acid; from α-nonyl acrolein; from methyl nonyl ketone and ethyl monochloroacetate in the presence of sodium ethylate

Metabolism

See monograph on aldehyde C-8*.